Thiazole → HCID 178451152, compound

Temperature

-78 °C

A solution of thiazole (800 mg, 9.40 mmol) in THF (94 mL) was cooled to −78° C. nBuLi (2.5 M in THF, 3759 μl, 9.40 mmol) was added and the solution was stirred for 30 minutes at −78° C. Butyl cis-4-acetylcyclohexanecarboxylate (2552 mg, 11.28 mmol) in THF (5 mL) was added in one portion and the solution was stirred for one hour at −78° C. The reaction was diluted with water and then warmed to room temperature. The mixture was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (5-30% ethyl acetate/hexanes) to afford cis-butyl 4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate. MS ESI calc'd. for C16H25NO3S [M+H+] 312. found 312.

1. additionwas added
2. stirringthe solution was stirred for one hour at −78° C
3. temperaturewarmed to room temperature
4. extractionThe mixture was extracted with ethyl acetate
5. dry with materialthe organic layer was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by column chromatography on silica gel (5-30% ethyl acetate/hexanes)

ORD record

ord-26c895a52e3d4aae92820065292b31a9

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120785B2